Iodine → 7-Iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinone

HRID 21102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21102
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:21].[K+].II.[N:25]([O:27]C(C)(C)C)=[O:26]>C(#N)C.[Cu](I)I>[I:21][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[C:16]([N+:25]([O-:27])=[O:26])[C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Komponenten

7

Edukt 4

HCID 807IodineHCID 4875Potassium IodideHCID 10906Tert-Butyl nitriteHCID 684876617-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone

Produkt 1

HCID 684887357-Iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinoneAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 4 of Example 140, 7-amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone (202 mg, 0.747 mmol) was dissolved in acetonitrile (10.1 mL), and the solution was treated with potassium iodide (149 mg, 0.896 mmol), copper iodide (171 mg, 0.896 mmol), iodine (228 mg, 0.896 mmol) and tert-butyl nitrite (0.266 mL, 0.896 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 7-iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinone (100 mg, yield 31%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-bdbbee7acee84f529f217d38b8790b81
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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